The activity of propolis in the scavenging of vitamin B2-photogenerated ROS

References

• Larson RA. The antioxidants of higher plants. Phytochemistry 1988;27:969–78. doi: 10.1016/0031-9422(88)80254-1
   Web of Science ®Google Scholar
• Hudson BJ. Food antioxidants. London: Elsevier Applied Food Science; 1990.
   Google Scholar
• Hall, III CA, Cuppett SL. Structure-activities of natural antioxidants. In: Aruoma O.I. and Cuppett S.L., (Eds.), Antioxidant methodology: In vivo and in vitro concepts. AOCS Press, Illinois; 1997. pp. 141–172.
   Google Scholar
• Branen AL. Toxicology and biochemistry of butylatedhydroxy anisole and butylatedhydroxy toluene. J Am Oil Chem Soc 1975;52:59–63. doi: 10.1007/BF02901825
   PubMed Web of Science ®Google Scholar
• Ito N, Fukushima S, Hasegawa A, Shibata M, Ogiso T. Carcinogenicity of butylatedhydroxy anisole in F344 rats. J Natl Cancer Inst 1983;70:343–7.
   PubMed Web of Science ®Google Scholar
• Löliger J. The use of antioxidants in foods. In: Aruoma OI, Halliwell B, (eds.) Free radicals and food additives. Taylor & Francis. London; 1991. pp. 121–50.
   Google Scholar
• Haung D, Ou B, Prior RL. The chemistry behind antioxidant capacity assays. J Agric Chem 2005;53:1841–56. doi: 10.1021/jf030723c
   PubMed Web of Science ®Google Scholar
• Asís M. El propóleo. Un valioso producto apícola. In: CIDA, (ed.) Propóleo. El oro púrpura de las abejas. Ministerio de la Agricultura. La Habana; 1991. pp. 53–71.
   Google Scholar
• Guerra AG, Méndez RB. Principales aplicaciones. In: de la Torriente P, (ed.) Propóleos, un camino hacia la salud. Ministerio de la Agricultura. La Habana; 1997. pp. 47–59.
   Google Scholar
• Farré R, Frasquet I, Sanchez A. Propolis and human health. Ars Pharmaceutica 2004;45:21–43.
   Google Scholar
• De Vecchi E, Drago L. Propolis’ antimicrobial activity: what's new? Infez Med 2007;15:7–15.
   PubMedGoogle Scholar
• Luo C, Zou X, Li Y, Sun C, Jiang Y, Wu Z. Determination of flavonoids in propolis-rich functional foods by reversed phase high performance liquid chromatography with diode array detection. Food Chem 2011;127:314–20. doi: 10.1016/j.foodchem.2011.01.006
   Web of Science ®Google Scholar
• Pietta PG. Flavonoids as antioxidants. J Nat Prod 2000;63:1035–42. doi: 10.1021/np9904509
   PubMed Web of Science ®Google Scholar
• Heelis PF. The photochemistry of flavins. In: Muller F, (ed.) Chemistry and biochemistry of flavoenzymes. (CRS Press: Boca Raton, FL); 1991. Vol 1.
   Google Scholar
• Takimoto K, Tano K, Hashimoto M, Hori M, Akasaka S, Utsumi H. Delayed transfection of DNA after riboflavin mediated photosensitization increases G: C to C: G transversions of supF gene in Escherichia coli mutY strain. Mutat Res 1999;445:93–8. doi: 10.1016/S1383-5718(99)00138-2
   PubMed Web of Science ®Google Scholar
• Yettella RR, Min DB. Effects of Trolox and ascorbic acid on the riboflavin photosensitized oxidation of aromatic amino acids. Food Chem 2010;118:35–41. doi: 10.1016/j.foodchem.2009.04.022
   Web of Science ®Google Scholar
• Heelis PF. The photophysical and photochemical properties of flavins (isoalloxazines). Chem Soc Rev 1982;11:15–39. doi: 10.1039/cs9821100015
   Web of Science ®Google Scholar
• Redmond RW, Gamlin JN. A compilation of singlet oxygen yields from biologically relevant molecules. Photochem Photobiol 1999;70:391–475. doi: 10.1562/0031-8655(1999)070<0391:ACOSOY>2.3.CO;2
   PubMed Web of Science ®Google Scholar
• Dzhagarov BM, Kruk NN, Konovalova NV, Solodunov AA, Stepuro II. Photosensitized formation of singlet oxygen by vitamins of the B group. J Appl Spectros 1995;62:285–9. doi: 10.1007/BF02606482
   Google Scholar
• Montaña MP, Pappano N, Debattista N, Ávila V, Posadaz A, Bertolotti SG, et al. The activity of 3- and 7-hydroxyflavones as scavengers of superoxide radical anion generated from photo-excited riboflavin. Can J Chem 2003;81:909–14. doi: 10.1139/v03-097
   Web of Science ®Google Scholar
• Montaña MP, Massad WA, Criado S, Biasutti A, García NA. Stability of flavonoids in the presence of riboflavin-photogenerated reactive oxygen species. A kinetic and mechanistic study on quercetin, morin and rutin. Photochem Photobiol 2010;86:827–34. doi: 10.1111/j.1751-1097.2010.00754.x
   PubMed Web of Science ®Google Scholar
• Agüero MB, González M, Lima B, Svetaz L, Sánchez L, Zacchino S, et al. Argentinean propolis from Zuccagnia punctata Cav. (Caesalpinieae) exudates: phytochemical characterization and antifungal activity. J Agric Food Chem 2010;58:194–201. doi: 10.1021/jf902991t
   PubMed Web of Science ®Google Scholar
• Szliszka E, Czuba ZP, Domino M, Mazur B, Zydowicz G, Krol W. Ethanolic extract of propolis (EEP) enhances the apoptosis-inducing potential of TRAIL in cancer cells. Molecules 2009;14:738–54. doi: 10.3390/molecules14020738
   PubMed Web of Science ®Google Scholar
• Kumazawa S, Hamasaka T, Nakayama T. Antioxidant activity of propolis of various geographic origins. Food Chem 2004;84:329–39. doi: 10.1016/S0308-8146(03)00216-4
   Web of Science ®Google Scholar
• Lima B, Tapia AA, Luna L, Fabani MP, Schmeda-Hirschmann G, Podio NS, et al. Main flavonoids, DPPH activity, and metal content allow determination of the geographical origin of propolis from the Province of San Juan (Argentina). J Agric Food Chem 2009;57:2691–8. doi: 10.1021/jf803866t
   PubMed Web of Science ®Google Scholar
• Ahn MR, Kumazawa S, Usui Y, Nakamura J, Matsuka M, Zhu F, et al. Antioxidant activity and constituents of propolis collected in various areas of China. Food Chem 2007;101:1383–92. doi: 10.1016/j.foodchem.2006.03.045
   Web of Science ®Google Scholar
• Tratniek PG, Hoigné J. Oxidation of substituted phenols in the environment: a QSAR analysis of rate constants for reaction with singlet oxygen. Environ Sci Technol 1991;25:1596–1604. doi: 10.1021/es00021a011
   Web of Science ®Google Scholar
• Criado S, Allevi C, Ceballos C, García NA. Visible-light-promoted degradation of the commercial antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT): a kinetic study. Redox Rep 2007;12:282–8. doi: 10.1179/135100007X239252
   PubMed Web of Science ®Google Scholar
• Wilkinson F, Helman WP, Ross A. Rate constants for the decay of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation. J Phys Chem Ref Data 1995;24:663–1021. doi: 10.1063/1.555965
   Web of Science ®Google Scholar
• Amat-Guerri F, García NA. Photodegradation of hydroxylated N-heteroaromatic derivatives in natural-like aquatic environments. A review of kinetic data of pesticide model compounds. Chemosphere 2005;59:1067–82. doi: 10.1016/j.chemosphere.2004.12.028
   PubMed Web of Science ®Google Scholar
• Fritz BJ, Matsui K, Kasai S, Yoshimura A. Triplet lifetime of some flavins. Photochem Photobiol 1987;45:539–41. doi: 10.1111/j.1751-1097.1987.tb05415.x
   Web of Science ®Google Scholar
• Gutiérrez S, Criado S, Bertolotti S, García NA. Dark and photoinduced interactions between Trolox, a polar-solvent-soluble model for vitamin E, and riboflavin. J Photochem Photobiol B 2001;62:133–9. doi: 10.1016/S1011-1344(01)00170-1
   PubMed Web of Science ®Google Scholar
• Wilkinson F, Helman WP, Ross AB. Quantum yields for the photosensitized formation of the lowest electronically excited singlet state of molecular oxygen in solution. J Phys Chem Ref Data 1993;22:133–262. doi: 10.1063/1.555934
   Web of Science ®Google Scholar
• García NA. Singlet molecular oxygen-mediated photodegradation of aquatic phenolic pollulants. A kinetic and mechanistic overview. J Photochem Photobiol B 1994;22:185–96. doi: 10.1016/1011-1344(93)06932-S
   Web of Science ®Google Scholar
• Escalada JP, Pajares A, Gianotti J, Massad W, Bertolotti S, Amat-Guerri F, et al. Dye-sensitized photodegradation of the fungicide carbendazim and related benzimidazoles. Chemosphere 2006;65:237–44. doi: 10.1016/j.chemosphere.2006.02.057
   PubMed Web of Science ®Google Scholar
• Silva E, Herrera L, Edwards AM, De La Fuente J, Lissi E. Enhancement of riboflavin-mediated photo-oxidation of glucose 6-phosphate dehydrogenase by uronic acid. Photochem Photobiol 2005;81:206–11. doi: 10.1562/2004-07-14-RA-233.1
   PubMed Web of Science ®Google Scholar
• Silva E, Edwards AM, Pacheco D. Visible light-induced photooxidation of glucose sensitized by riboflavin. J Nutr Biochem 1999;10:181–5. doi: 10.1016/S0955-2863(98)00093-X
   PubMed Web of Science ®Google Scholar
• Garcia J, Silva E. Flavin-sensitized photooxidation of amino acids present in a parenteral nutrition infusate: protection by ascorbic acid. J Nutr Biochem 1997;8:341–5. doi: 10.1016/S0955-2863(97)00024-7
   Web of Science ®Google Scholar
• Posadaz A, Biasutti A, Casale C, Sanz J, Amat-Guerriand F, García NA. Rose bengal-sensitized photooxidation of the dipeptides Trp-Phe, Trp-Tyr and Trp-Trp. Kinetics, mechanism and photoproducts. Photochem Photobiol 2004;80:132–8. doi: 10.1562/2004-03-03-RA-097.1
   PubMed Web of Science ®Google Scholar
• Montaña P, Pappano N, Debattista N, Ávila V, Posadaz A, Bertolotti SG, et al. The activity of 3- and 7-hydroxyflavones as scavengers of superoxide radical anion generated from photo-excited riboflavin. Can J Chem 2003;81:909–14. doi: 10.1139/v03-097
   Web of Science ®Google Scholar
• Spikes JD, Shen HR, Kopeccková P, Kopecek J. Photodynamic crosslinking of proteins. III. Kinetics of the FMN- and rose bengal-sensitized photooxidation and intermolecular crosslinking of model tyrosine-containing N-(2-Hydroxypropyl) methacrylamide copolymers. Photochem Photobiol 1999;70:130–7. doi: 10.1111/j.1751-1097.1999.tb07980.x
   PubMed Web of Science ®Google Scholar